Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties

Kenichi Matsuda; Shinya Niikura; Rintaro Ichihara; Kei Fujita; Anna M. Strasser; Rokusuke Yoshikawa; Jiro Yasuda; Yoshiki Hiramatsu; Hironori Hayashi; Eiichi N. Kodama; Toshiyuki Wakimoto

doi:10.1248/cpb.c24-00533

Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties

Kenichi Matsuda, Shinya Niikura, Rintaro Ichihara, Kei Fujita, Anna M. Strasser, Rokusuke Yoshikawa, Jiro Yasuda, Yoshiki Hiramatsu, Hironori Hayashi, Eiichi N. Kodama, Toshiyuki Wakimoto

IRIDeS - Disaster Medical Science Division

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH₂ enhance cytotoxicity.

Original language	English
Pages (from-to)	826-830
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	72
Issue number	9
DOIs	https://doi.org/10.1248/cpb.c24-00533
Publication status	Published - 2024 Sept

Keywords

acylation
cyclic peptide
non-ribosomal peptide

Access to Document

10.1248/cpb.c24-00533

Cite this

@article{185d52bb6bee4cf7bec81dc38d015c4d,

title = "Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties",

abstract = "Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH2 enhance cytotoxicity.",

keywords = "acylation, cyclic peptide, non-ribosomal peptide",

author = "Kenichi Matsuda and Shinya Niikura and Rintaro Ichihara and Kei Fujita and Strasser, \{Anna M.\} and Rokusuke Yoshikawa and Jiro Yasuda and Yoshiki Hiramatsu and Hironori Hayashi and Kodama, \{Eiichi N.\} and Toshiyuki Wakimoto",

note = "Publisher Copyright: {\textcopyright} 2024 Author(s)",

year = "2024",

month = sep,

doi = "10.1248/cpb.c24-00533",

language = "English",

volume = "72",

pages = "826--830",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "9",

}

TY - JOUR

T1 - Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties

AU - Matsuda, Kenichi

AU - Niikura, Shinya

AU - Ichihara, Rintaro

AU - Fujita, Kei

AU - Strasser, Anna M.

AU - Yoshikawa, Rokusuke

AU - Yasuda, Jiro

AU - Hiramatsu, Yoshiki

AU - Hayashi, Hironori

AU - Kodama, Eiichi N.

AU - Wakimoto, Toshiyuki

PY - 2024/9

Y1 - 2024/9

N2 - Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH2 enhance cytotoxicity.

AB - Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH2 enhance cytotoxicity.

KW - acylation

KW - cyclic peptide

KW - non-ribosomal peptide

UR - http://www.scopus.com/inward/record.url?scp=85204373771&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85204373771&partnerID=8YFLogxK

U2 - 10.1248/cpb.c24-00533

DO - 10.1248/cpb.c24-00533

M3 - Article

C2 - 39313387

AN - SCOPUS:85204373771

SN - 0009-2363

VL - 72

SP - 826

EP - 830

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 9

ER -

Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this